CA2940269C - Mitochondrial aldehyde dehydrogenase 2 (aldh2) binding polycyclic amides and their use for the treatment of cancer - Google Patents

Mitochondrial aldehyde dehydrogenase 2 (aldh2) binding polycyclic amides and their use for the treatment of cancer Download PDF

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CA2940269C
CA2940269C CA2940269A CA2940269A CA2940269C CA 2940269 C CA2940269 C CA 2940269C CA 2940269 A CA2940269 A CA 2940269A CA 2940269 A CA2940269 A CA 2940269A CA 2940269 C CA2940269 C CA 2940269C
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CA2940269A1 (en
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Wenjin Yang
Teh-Yie YU
Chun Jiang
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Aviv Therapeutics Inc
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Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3490613A4 (en) * 2016-07-26 2020-03-04 Cornell University GENE THERAPY FOR THE TREATMENT OF ALDEHYDE DEHYDROGENASE DEFICIT
WO2018204673A1 (en) * 2017-05-05 2018-11-08 The Board Of Trustees Of The Leland Stanford Junior University Methods and compositions for treating endometriosis and endometriosis associated symptoms
CN108929263B (zh) * 2017-05-26 2022-07-22 中国医学科学院药物研究所 芳酰胺类Kv2.1抑制剂及其制备方法、药物组合物和用途
WO2019055169A1 (en) * 2017-09-15 2019-03-21 The Board Of Trustees Of The Leland Stanford Junior University MITOCHONDRIAL ALDEHYDE DEHYDROGENASE 2 MODULATORS FOR THE PROTECTION, EXPANSION AND INCREASE IN THE POWER OF HEMATOPOIETIC STEM CELLS
WO2019079209A1 (en) * 2017-10-16 2019-04-25 Amygdala Neurosciences, Inc. POLYTHERAPY FOR THE PREVENTION OF AN ADDICTION
CN108376559B (zh) * 2018-02-28 2020-10-16 复旦大学附属中山医院 乙醛脱氢酶2基因型在麻醉剂量计算中的应用
CN112638881A (zh) * 2018-07-31 2021-04-09 普林斯顿大学托管委员会 用于治疗转移性和化疗耐受性癌症的四氢喹啉衍生物
CA3168533A1 (en) * 2020-01-24 2021-07-29 The Trustees Of Princeton University Heterocyclic compounds and uses thereof
KR102460570B1 (ko) 2020-02-18 2022-10-28 주식회사 피코엔텍 신규한 돌연변이 효모를 함유하는 아토피 억제 조성물
AR123971A1 (es) * 2020-11-02 2023-02-01 Alchemedicine Inc Compuesto, agente de activación de aldehído deshidrogenasa 2, composición farmacéutica y fármaco terapéutico y/o profiláctico
WO2022226383A1 (en) 2021-04-22 2022-10-27 Kayothera Inc. Heterocyclic compounds and uses thereof
WO2023146274A1 (ko) 2022-01-26 2023-08-03 서울대학교병원 알데히드 탈수소효소 2 조절을 통한 탈모 또는 백모의 예방, 개선, 또는 치료용 조성물
CN118591526A (zh) * 2022-04-22 2024-09-03 亚克医药株式会社 化合物、乙醛脱氢酶2激活剂、药物组合物以及治疗及/或预防药
WO2023244574A1 (en) 2022-06-14 2023-12-21 Amygdala Neurosciences, Inc. Aldh-2 inhibitor compounds and methods of use

Family Cites Families (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW197439B (ko) 1991-04-04 1993-01-01 Ueno Pharmaceutics Applic Res Co Ltd
US5283253A (en) 1991-09-23 1994-02-01 Florida State University Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them
WO1993010076A1 (en) 1991-11-22 1993-05-27 The University Of Mississippi Synthesis and optical resolution of the taxol side chain and related compounds
US5200534A (en) 1992-03-13 1993-04-06 University Of Florida Process for the preparation of taxol and 10-deacetyltaxol
JPH08500973A (ja) 1992-05-21 1996-02-06 ザ ペン ステイト リサーチ ファウンデーション タキソール、関連タキサン及び他の新規な抗癌/抗ウイルス性化合物原料としてのイチイ培養組織
US5274137A (en) 1992-06-23 1993-12-28 Nicolaou K C Intermediates for preparation of taxols
US5294637A (en) 1992-07-01 1994-03-15 Bristol-Myers Squibb Company Fluoro taxols
US5202448A (en) 1992-08-14 1993-04-13 Napro Biotherapeutics, Inc. Processes of converting taxanes into baccatin III
CA2100808A1 (en) 1992-10-01 1994-04-02 Vittorio Farina Deoxy paclitaxels
FR2696461B1 (fr) 1992-10-05 1994-11-10 Rhone Poulenc Rorer Sa Nouveaux dérivés d'analogues du taxol, leur préparation et les compositions qui les contiennent.
FR2696458B1 (fr) 1992-10-05 1994-11-10 Rhone Poulenc Rorer Sa Procédé de préparation de dérivés du taxane.
FR2696463B1 (fr) 1992-10-05 1994-11-25 Rhone Poulenc Rorer Sa Procédé d'obtention de la désacétyl-10 baccatine III.
FR2696464B1 (fr) 1992-10-05 1994-11-10 Rhone Poulenc Rorer Sa Nouveau procédé d'estérification de la baccatine III et de la désacétyl-10 baccatine III.
FR2696462B1 (fr) 1992-10-05 1994-11-25 Rhone Poulenc Rorer Sa Procédé d'obtention de la désacétyl-10 baccatine III.
US5279949A (en) 1992-12-07 1994-01-18 Board Of Trustees Operating Michigan State University Process for the isolation and purification of taxol and taxanes from Taxus spp
US5824701A (en) 1993-10-20 1998-10-20 Enzon, Inc. Taxane-based prodrugs
US5415869A (en) 1993-11-12 1995-05-16 The Research Foundation Of State University Of New York Taxol formulation
WO1998008833A1 (en) 1996-08-26 1998-03-05 Bristol-Myers Squibb Company Sulfenamide taxane derivatives
AU739028B2 (en) 1996-09-27 2001-10-04 Bristol-Myers Squibb Company Hydrolyzable prodrugs for delivery of anticancer drugs to metastatic cells
WO1998022451A1 (fr) 1996-11-19 1998-05-28 Daiichi Pharmaceutical Co., Ltd. Derives taxol
US5977386A (en) 1996-12-24 1999-11-02 Bristol-Myers Squibb Company 6-thio-substituted paclitaxels
WO1998058927A1 (en) 1997-06-20 1998-12-30 Baker Norton Pharmaceuticals, Inc. Soluble prodrugs of paclitaxel
US7288665B1 (en) 1997-08-18 2007-10-30 Florida State University Process for selective derivatization of taxanes
JPH1192468A (ja) 1997-09-17 1999-04-06 Yakult Honsha Co Ltd 新規なタキサン誘導体
WO1999018113A1 (fr) 1997-10-08 1999-04-15 Bio Research Corporation Of Yokohama Derives taxoides et leur procede de production
FR2847253B1 (fr) * 2002-11-19 2007-05-18 Aventis Pharma Sa Nouveaux derives de pyridazinones a titre de medicaments et compositions pharmaceutiques les renfermant
CA2548254A1 (en) 2003-12-09 2005-06-23 The Board Of Trustees Of The Leland Stanford Junior University Methods and compositions for modulating mitochondrial aldehyde dehydrogenase-2
CN101111479A (zh) * 2004-12-16 2008-01-23 沃泰克斯药物股份有限公司 可用作激酶抑制剂的吡啶酮
RU2423351C2 (ru) * 2004-12-16 2011-07-10 Вертекс Фармасьютикалз Инкорпорейтед Пирид-2-оны, применимые как ингибиторы протеинкиназ семейства тес для лечения воспалительных, пролиферативных и иммунологически-опосредованных заболеваний
KR20090117950A (ko) * 2007-03-08 2009-11-16 더 보드 오브 트러스티스 오브 더 리랜드 스탠포드 쥬니어 유니버시티 미토콘드리아 알데히드 탈수소효소-2 조절자 및 그것의 사용 방법
KR20110082180A (ko) * 2008-10-28 2011-07-18 더 보드 오브 트러스티스 오브 더 리랜드 스탠포드 쥬니어 유니버시티 알데히드 탈수소효소의 조절자 및 그것의 사용방법
CN102600182B (zh) * 2012-03-05 2013-09-11 浙江工业大学 苯乙酰氟苯水杨酰胺类化合物在制备抗肺癌药物中的应用
CN102614198B (zh) * 2012-03-05 2014-05-14 浙江工业大学 (4-取代苯甲酰)氟苯水杨酰胺类化合物在制备抗肺癌药物中的应用
US9670162B2 (en) * 2013-03-14 2017-06-06 The Board Of Trustees Of The Leland Stanford Junio Mitochondrial aldehyde dehyrogenase-2 modulators and methods of use thereof
CN103880700B (zh) * 2014-03-14 2016-05-18 浙江工业大学 O-肉桂酰-氟苯水杨酰胺类化合物及其在制备抗宫颈癌药物中的应用

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